Skip to main content
SpringerLink
Log in
Book cover

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products pp 71–152Cite as

Carbazole Alkaloids III

  • Chapter

Abstract

Major developments in the chemistry of carbazoles until 1960 arose mainly as a result of their use in the dye stuff and polymer industries although carbazole itself (1) was discovered in coal tar in 1872 by Graebe and Glazer (53). Since the report of the first carbazole alkaloid murrayanine (2) from Murraya koeinigii Spreng and the antibiotic properties of these alkaloids in 1965 by Chakraborty et al. (22, 31), there has been wider interest on the structure, synthesis and biochemical properties of these compounds. At present more than one hundred alkaloids are known and various biochemical and medicinal properties of this group of compounds have been investigated. Several reviews relating to carbazole alkaloids have appeared since 1971 (67,18, 19, 20, 56, 11). The present review relates to work reported after the previous review (11) and earlier results not included therein.

Part I—Ref. (18); Part II—Ref. (11).

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Akugin, E., and U. Pindur: Chemische Eigenschaften und Synthese-Verfahren von 3-Vinylindolen. J. Heterocyclic Chem. 22, 585 (1985).

    Google Scholar 

  2. Albrecht, W.L., and R.W. Fleming: Bis-basic Esters and Amides of Carbazoles. US. 3932456 (C.A. 84, 150499t, 1976 ).

    Google Scholar 

  3. Al-Ekabi, H., and P. De Mayo: The Cds Photo-induced Dimerisation of N-Vinyl Carbazoles. Tetrahedron 42, 6277 (1986).

    CAS  Google Scholar 

  4. Ascalone, V., and L. Dalbo: Rapid and Simple Detection of Carpofen in Plasma by HPLC with Fluorescence Detection. J. Chromatography 276, 230 (1983).

    CAS  Google Scholar 

  5. Banderanayake, M., M.J. Begeley, B.O. Brown, D.G. Clarke, L. Crombie, and D.A. Whiting: Synthesis of Acridone and Carbazole Alkaloids Involving Pyridine Catalysed Chromene Formation: Crystal and Molecular Structure of Dibromocannabicyclol and Its Bearing on the Structures of Cyclol Alkaloids. J. Chem. Soc. Perkin I, 999 (1974).

    Google Scholar 

  6. Beecham Group: Antiemetics. J.P. 61 21252/1986 (C.A. 106, 78, 761 g, 1987 ).

    Google Scholar 

  7. Bergman, J., and B. Pelcman: Synthesis of Carbazoles Related to Carbazomycin, Hyellazole and Ellipticine. Tetrahedron 44, 5215 (1988).

    CAS  Google Scholar 

  8. Bergman, J., and R. Carlson: A Novel Synthesis of 2-Amino and 2-Hydroxycarbazoles. Tetrahedron Letters 4051 (1978).

    Google Scholar 

  9. Bhattacharyya, L., S.K. Roy, and D.P. Chakraborty: Structure of the Carbazole Alkaloid Isomurrayazoline from Murraya koenigii Spreng. Phytochem. 21, 2432 (1982).

    Google Scholar 

  10. Bhattacharyya, L., S. Roy, S. Chatterjee, and D.P. Chakraborty: Murrayazolinol—A Minor Carbazole Alkaloid from Murraya koenigii Spreng. J. Indian Chem. Soc. 66, 140 (1989)

    CAS  Google Scholar 

  11. Bhattacharyya, P., and Chakraborty, D.P.: Carbazole Alkaloids. In: Fortschr. Chem. Organ. Naturstoffe, Vol. 52, pp 159. ( W. Herz, H. Grisebach, and G.W. Kirby, Eds.) Wien, N.Y.: Springer 1987.

    Google Scholar 

  12. Bhattacharyya, P., M. Sarkar, A.K. Biswas, and D.P. Chakraborty: Iodine Promoted Thermal Cyclisation of Anthranilic acid. J. Indian Chem. Soc. 46, 328 (1979).

    Google Scholar 

  13. Birch, A.J., A.J. Leipa, and G.R. Stephenson: Organometallic Compounds in Organic Synthesis: Some Tricarbonyl (Cyclohexadienyl) Iron Cations and Nitrogen Containing Nucleophiles. Tetrahedron Letters 3565 (1979).

    Google Scholar 

  14. Bisset, N.G., A.K. Choudhury, and M.D. Walker: Occurrence of N-Cyano Alkaloids in Asian Strychnos Species. Phytochem. 13, 255 (1974).

    CAS  Google Scholar 

  15. Canas-Rodriquez, A., and A. Mateo-Barnardo: Tetrahydrocarbazoles: Part-II. Tricyclic Inhibitors of Gastric acid Secretion. An. Quim. Ser. C. 81 254 (1985).

    Google Scholar 

  16. Chakrabarti, A., and D.P. Chakraborty: Photochemical Rearrangement of Pyranocarbazole Alkaloids: Part 1. Tetrahedron Letters 29, 6625 (1988).

    CAS  Google Scholar 

  17. Chakrabarti, A., and D.P. Chakraborty: Novel Access to Bis-Carbazoles Alkaloids: Substituent Effect on the Efficiency and Regioselectivity in BF3–Et20 Mediated Intermolecular coupling of Pyranocarbazole Alkaloids. Tetrahedron 45 7007 (1989).

    Google Scholar 

  18. Chakrabarti, A., G.K. Biswas, and D.P. Chakraborty: Photo-Fries Rearrangement in N-Sulphonyl Carbazoles. Tetrahedron 45, 5059 (1989).

    CAS  Google Scholar 

  19. Chakraborty, D.P.: Carbazole Alkaloids. In: Fortschr. Chem. Organ. Naturstoffe, Vol. 34, pp. 299 (W. Herz, H. Grisebach, and G.W. Kirby, Eds.) Wien-New York, Springer: 1977.

    Google Scholar 

  20. Chakraborty, D.P.: Some Aspects of Carbazole Alkaloids. Planta Medica 39, 97 (1980).

    CAS  Google Scholar 

  21. Chakraborty, D.P.: Twenty Years of Carbazole Alkaloids. Trans. Bose. Res. Inst. 47 49 (1984).

    Google Scholar 

  22. Chakraborty, D.P.: Some Newer Aspects of Plant Alkaloids. J. Indian Chem. Soc. 66 843 (1989).

    CAS  Google Scholar 

  23. Chakraborty, D.P., B.K. Barman, and P.K. Bose: On the Constitution of Murrayanine, a Carbazole Derivative Isolated from Murraya koenigii Spreng. Tetrahedron 21 681 (1965).

    CAS  Google Scholar 

  24. Chakraborty, D.P., S. Roy, and A.K. Dutta: Thermal Synthesis of Nor-girinimbine and Its Linear Isomer: A New Synthesis of Girinimbine. J. Indian Chem. Soc. 64 215 (1987).

    CAS  Google Scholar 

  25. Chowdhury, B.K., A. Mustafa, M. Garba, and P. Bhattacharyya: Carbazole and 3-Methylcarbazole from Glycosmis pentaphylla. Phytochem. 26 2138 (1988).

    Google Scholar 

  26. Coats, I.H., J.A. Bell, D.C. Humber, and G.B. Ewan: Tetrahydrocarbazolone Derivatives, E.P.191562 (CA. 105 226579u, 1986).

    Google Scholar 

  27. Coats, I.H., J.A. Bell, D.C. Humber, and G.B. Ewan:Substituted (Imidazolylmethyl)carbazolones as 5-Hydroxytryptamine Antagonists, Their Preparations and Pharmaceutical Formulation. E.P. 210840 (C.A. 106 15675b, 1987).

    Google Scholar 

  28. Cone, M.C., P.J. Seaton, K.A. Halles, and S.J. Gould: New Products Related to Kinamycin from Streptomyces murrayamaensis: Taxonomy, Production, Isolation and Biological Properties. J. Antibiotics 42, 179 (1989).

    CAS  Google Scholar 

  29. Das, B.P.: Some Investigations of the Pesticidal Properties of Carbazoles. International Pest Control 31, 144 (1989).

    CAS  Google Scholar 

  30. Das, B.P., and B. Chowdhury: Search for Potential Larvicides from Carbazoles. Trans. Bose Inst. 47 91 (1984).

    CAS  Google Scholar 

  31. Das, B.: Ph.D. Thesis, Calcutta University 1982.

    Google Scholar 

  32. Das, K.C., D.P. Chakraborty, and P.K. Bose: Antifungal Activity of Some Constituents of Murraya koenigii Spreng. Experientia 21, 340 (1965).

    CAS  Google Scholar 

  33. Dean, F.M.: Natural Coumarins. In: Fortschr. Chem. Organ. Naturstoffe, Vol. 9, pp. 225 ( L. Zechmeister, Ed.) Wien: Springer. 1952.

    Google Scholar 

  34. Dewar, D., V. Glover, J. Elsworth, and M. Sandler: Equal and Other compounds from Bovine Urine as Monoamine Oxidase Inhibitors. J. Neural. Trans. 65, 147 (1986) (C.A. 105 72468t, 1986).

    CAS  Google Scholar 

  35. Dobson, R.L.M., A.P. Dsilva, S.J. Weeks, and V.A. Fassel: Multidimensional Laser-based Instrument for Characterisation of Environmental Samples for Poly-cyclic Aromatic Compounds. Anal. Chem. 58, 2129 (1986).

    CAS  Google Scholar 

  36. Domanski, A., and J.B. Kyz1ol: Synthesis of Bis-Basic Substituted 9-ethylcarbazoles. Pol. J. Chem. 59, 613 (1985).

    CAS  Google Scholar 

  37. El-Gazzar, M.A., A.M. El-Naggar, F.S.M. Ahmed, and A.M. Abdelsalem: Synthesis and Biological Activity of Some New Substituted Aminoacyl Carbazole Derivatives. Arab. Galf. J. Sci. Res. 1, 131 (1983) (C.A. 100, 19 2230c, 1984 ).

    Google Scholar 

  38. Ferris, R.M.: Treatment of Drug Induced Psychosis. U.S. US 4588728 (C.A. 105, 54624m, 1986 ).

    Google Scholar 

  39. Ferris, R.M., F.L.M. Tang, K.J. Chang, and A. Russel: Evidence that the Potential Antipsychotic Agent Rincazole (BW234 U) is Specific Competitive Antagonist of Sigma Sites in Brain. Life Science 38, 2329 (1986).

    CAS  Google Scholar 

  40. Ferris, R.M., H.L. White, F.L.M. Tang, A. Russel, and M. Harfenist: Rincazole (BW234 U) Novel Antipsychotic Agent Whose Mechanism of Action Cannot be Explained by a Direct Blockade of Postsynaptic Dopaminergic Receptors in Brain. Drug. Der. Res. 9, 171 (1987) (C.A. 106, 27732j, 1987 ).

    Google Scholar 

  41. Filimonov, V.D., T.A. Filippova, V.P. Lopatinskii, M.M. Sukhoroslova, and N.V. Stepanov: Carbon 13-NMR of N-substituted carbazoles. Transfer of Electronic Effects of Substituents Through Nitrogen to Carbazole Ring. Khim. Geterotsiki Soedin 9, 1184 (1988) (C.A. 106, 195772r, 1987 ).

    Google Scholar 

  42. Furukawa, H., C. Ito, M. Yogo, and T.S. Wu: Structures of Murrayastine, Murrayaline and Pyrayafoline: Three New Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 33, 1320 (1985).

    CAS  Google Scholar 

  43. Furukawa, H., M. Yogo, C. Ito, T.S. Wu, and C. Kuoh: New Carbazoloquinones Having Dimethyl Pyran Ring System. Chem. Pharm. Bull. 33, 1320 (1985).

    CAS  Google Scholar 

  44. Furukawa, H., T.S. Wu, and C. Kuoh: Dihydroxygirinimbine, a new Carbazole Alkaloid from Murraya euchrestifolia. Heterocycles 23, 1391 (1985).

    CAS  Google Scholar 

  45. Furukawa, H., T.S. Wu, and C. Kuoh: Structures of Murrafoline -B and -C, New Binary Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 33, 12611 (1985).

    Google Scholar 

  46. Furukawa, H., T.S. Wu, and T. Ohta: Bismurrayafoline-A and -B, Two Novel “Dimeric” Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 31, 4202 (1983).

    CAS  Google Scholar 

  47. Furukawa, H., T.S. Wu, T. Ohta, and S. Kuoh: Chemical Constituents of Murraya euchrestifolia Hayata, Structures of Novel Carbazolquinones and Other Carbazole Alkaloids. Chem. Pharm. Bull. 33, 4132 (1985).

    CAS  Google Scholar 

  48. Furusaki, A., M. Matsui, T. Watanabe, S. Omura, A. Nakagawa, and T. Hata: The Crystal and Molecular Structure of Kinamycin C p-Bromobenzoate. Israel J. Chem. 10, 173 (1972).

    CAS  Google Scholar 

  49. Gallagher, T., and P. Magnus: New Methods for Alkaloid Synthesis. Generation of Indole-2,3-Diquinomethanes as a Route to Indole Alkaloids. Tetrahedron 37, 3889 (1981).

    CAS  Google Scholar 

  50. Ghosh, S., T.K. Das, D.B. Datta, and S. Mehta: Studies on Enamides Part-1: Photochemical Rearrangement of N-Aroyl Carbazoles. Tetrahedron Letters 28, 4611 (1987).

    CAS  Google Scholar 

  51. Glaxo Group: Preparation of Tetrahydrocarbazole Derivatives as Serotonin Antagonists. Jr. Eur. Pat. Appl., E.P. 219, 193/1986 (C.A. 107 176032d, 1987) and previous references.

    Google Scholar 

  52. Griffith, W.P., S.V. Ley, G.P. Whitocomb, and A.D. White: Preparation and Use of tetra n-butylammonium Perruthenate (TBAP reagent) and Tetra-n-Propylammonium Perruthenate (TPAP reagent) as New Catalytic Oxidants for Alcohols. J.C.S. Chem. Commun. 1625 (1987).

    Google Scholar 

  53. Grellmann, K.H., and U. Schmitt: Reactivity and Decay Pathways of Photo-excited Anilino-naphthalene. J. Amer. Chem. Soc. 104, 6267 (1982).

    CAS  Google Scholar 

  54. Graebe, C., and C. Glazer: Ueber Carbazol. Chem. Ber. 5, 12 (1872).

    Google Scholar 

  55. Hata, T., S. Omura, Y. Iwai, A. Nakagawa, M. Otani, S. Ito, and T. Matsuya: A New Antibiotic Kinamycin. Fermentation, Isolation, Purification and Properties. J. Antibiotics 24, 353 (1971).

    CAS  Google Scholar 

  56. Hausberg, H.H., and H. Bettcher: Tetrahydrocarbazole Derivatives. Ger. Pat. DE 3,30094 (C.A. 101, 210979f, 1984 ).

    Google Scholar 

  57. Husson, H.: Simple Indole Alkaloids Including 13-Carbolines and Carbazoles In: Alkaloids, Vol. 26, pp. 1 ( Arnold Brossi Ed.) New York: Academic Press. 1985.

    Google Scholar 

  58. Ignatiadis, I., M. Kuroki, and P.J. Appino: Identification of Carbazole Derivatives in a Hydro Treated Gas Oil by Gas Chromatography and Gas Chromatography-Mass Spectrophotometry. J. Chromatography 366, 251 (1986).

    CAS  Google Scholar 

  59. Ito, C., T. Wu, and H. Furukawa: Three New Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 35, 450 (1987).

    CAS  Google Scholar 

  60. Ito, C., T. Wu, and H. Furukawa: New Carbazole Alkaloids from Murraya euchrestifolia. Chem. Pharm. Bull. 36, 2377 (1988).

    CAS  Google Scholar 

  61. Ito, C., T. Wu, and H. Furukawa: The Structures of Some New Carbazole Alkaloids. IUPAC Symp. New Delhi, Feb. 4–7, 1990, p. 259.

    Google Scholar 

  62. Ito, S., T. Matsuya, S. Omura, M. Otani, A. Nakagawa, Y. Iwai, M. Ohtani, and T. Hata: A New Antibiotic, Kinamycin. J. Antibiotics 23, 315 (1970).

    CAS  Google Scholar 

  63. Jackson, G.D.F., and W.H.F. Sasse: Synthetical Applications of Activated Metal Catalysts. XXI. The Formation of Carbazole from Aniline and Related Compounds in Presence of Degassed Raney Nickel. Austr. J. Chem. 17, 347 (1964).

    CAS  Google Scholar 

  64. Joule, J.: Recent Advances in 9H Carbazoles. In: Advances in Heterocyclic Chemistry, Vol. 35, pp. 83. ( A. Katritzky Ed.) New York: Academic Press 1984.

    Google Scholar 

  65. Kamaruzzaman, S. Roy, and D.P. Chakraborty: Mumpamine from Glycosmis pentaphylla. Phytochem. 28, 677 (1989).

    Google Scholar 

  66. Kane, V., A.R. Martin, and P.A. Peters: The Non-regiospecific Condensation of Citral and 2-Hydroxycarbazole. Heterocycles 16, 1445 (1981).

    CAS  Google Scholar 

  67. Kaneda, M., T. Naid, T. Kitahara, and S. Nakamura: Carbazomycin G and H, Novel Carbazomycin Congeners Containing a Quinol Moiety. J. Antibiotics 41, 602 (1988).

    CAS  Google Scholar 

  68. Kapil, R.S.: Carbazole Alkaloids. In: Alkaloids, Vol. 13, pp. 273. ( R.H.F. Manske, Ed.) New York, London, Academic Press. 1971.

    Google Scholar 

  69. Karmakar, T., M. Mukherjee, and D.P. Chakraborty: Some Urea Derivatives as Growth Inhibitors. Curr. Sci. 55, 828 (1986).

    CAS  Google Scholar 

  70. Katritzky, A.R., G.W. Rewcastle, and L.M.V. De Miguel. Improved Syntheses of Substituted Carbazoles and Benzocarbazoles via Lithiation of the (Dialkylamino) methyl (Aminal) Derivatives. J. Org. Chem. 53, 794 (1988).

    CAS  Google Scholar 

  71. Kawasaki, T., Y. Nonaka, and M. Sakamoto: A New Efficient Synthesis of the 3Methoxy Carbazole Alkaloid Hyellazole. J. Chem. Soc. Chem. Commun. 43 (1989).

    Google Scholar 

  72. Kedderis, G.L., D.E. Douglas, R.N. Pandey, and P.F. Hollenberg: Oxygen-l8Studies of Peroxidase Catalysed N-Methyl Carbazole. Mechanism of Carbinolamine and Carboxyaldehyde Formation. J. Biol. Chem. 261, 15910 (1986).

    CAS  Google Scholar 

  73. Khazipov, R. Kh., R. Kh. Almaev, T.V. Korobova, and F.D. Davlyatov: Prevention of Growth of Bacteria. USSR Su 1212972 (C.A. 105 149668 t, 1986 ).

    Google Scholar 

  74. Knölker, H., and M. Bauermeister: The Total Synthesis of Carbazole Antibiotic Carbazomycin B and an Improved Route to Carbazomycin A. J. Chem. Soc. Chem. Commun. 1468 (1989).

    Google Scholar 

  75. Kondo, S., M. Katayama, and S. Marumo: Carbazomycinal and 6-Methoxycarbazomycinal as Aerial Mycellium Formation Inhibitory Substances of Streptoverticillium species. J. Antibiotics 39, 727 (1986).

    CAS  Google Scholar 

  76. Lontsi, D., J.F. Ayafor, B.L. Sondengam, J.D. Conolly, and D.S. Rycroft: The Use of Two Dimensional Proton Coupled 13C-NMR Spectrum in the Structural Elucidation of Ekebergenine, a New Carbazole Alkaloid from Ekebergia senegenalensis (Meliaceae). Tetrahedron Letters 26 4249 (1985).

    CAS  Google Scholar 

  77. Luk, K., L. Stern, M. Weigel, R.A. O’Brien, and N. Spirt: Isolation and Identification of `Diazepam Like’ Compounds from Bovine Urine. J. Nat. Prod. 46, 852 (1983).

    CAS  Google Scholar 

  78. Lednicer, D., and L.A. Mitcher: In: The Organic Chemistry of Drug Synthesis, vol. 3, pp. 168. New York: John Wiley & Sons. 1984.

    Google Scholar 

  79. Ljunggren, Bo, and K. Lundberg: In Vivo Phototoxicity of Nonsteroidal Antiinflammatory Drugs Evaluated by the Mousetail Technique: Photodermatology 2 377 (1985) (C.A. 104 81699 a, 1986).

    Google Scholar 

  80. Martin, T., and C.J. Moody: A New Route to 1-oxygenated Carbazoles. Synthesis of Murrayafoline-A. Tetrahedron Letters 26, 5841 (1985).

    CAS  Google Scholar 

  81. Masaki, M.T., S. Yushiro, S. Tsutomu, and N. Keiju: Pharmacological Studies on Carpofen, a New Non-steroidal Anti-inflammatory Drug in Animals. Nippon Kagaku Zasshi 73, 757 (1977) (C.A. 88, 69038c, 1978 ).

    Google Scholar 

  82. Mcphail, A.T., T.S. Wu, T. Ohta, and H. Furukawa: Structure of (±) Murrafoline, a Novel Biscarbazole Alkaloid from Murraya euchrestifolia. Tetrahedron Letters 24, 5377 (1983).

    CAS  Google Scholar 

  83. Mitra, A.R.: Ph.D. Thesis, Calcutta University, 1974.

    Google Scholar 

  84. Mobilio, D., C.A. Demeerson, and L.G. Humber: Substituted 2,3,4,9-Tetrahydro1-H-Carbazole-1-acetic acid and Its Use. US US4584312 (C.A. 105 133743c, 1986) and previous ref.

    Google Scholar 

  85. Moody, C.J., and P. Shah: Diels-Alder Reactivity of Pyrano [3,4-b] Indol-3-ones Part 4, Synthesis of Alkaloids Carbazomycin A, B, and Hyellazole. J.C.S. Parkin Trans 1, 2463 (1989).

    Google Scholar 

  86. Ngadjui, B.T., J.F. Ayafor, B.L. Sondengam, and J.D. Connolly: Quinolone and Carbazole Alkaloids from Clausena anisata. Phytochem. 28 1517 (1989).

    CAS  Google Scholar 

  87. Naid, T., T. Kitahara, M. Kaneda, and S. Nakamura: Carbazomycins C, D, E, F and G. Minor Components of Carbazomycins. J. Antibiotics 40, 157 (1987).

    CAS  Google Scholar 

  88. Narashimhan, N.S., and S.L. Kelkar: Alkaloids of Murraya koenigii Part III. Structure of Currayanine and Currayangine. Ind. J. Chem. 14B, 430 (1976).

    Google Scholar 

  89. Omura, S., A. Nakagawa, H. Yamada, T. Hata, A. Furusaki, and T. Watanabe: Structure of Kinamycin C and the Structural Relations Among Kinamycins A, B, C, D. Chem. Pharm. Bull. 19, 2428 (1971).

    CAS  Google Scholar 

  90. Omura, S., A. Nakagawa, H. Yamada, T. Hata, A. Furusaki, and T. Watanabe: Structures and Biological Properties of Kinamycin A, B, C, D. Chem. Pharm. Bull. 21, 931 (1973).

    CAS  Google Scholar 

  91. Padwa, A., and J.A. Lee: Photochemical Transformations of 2,2-Disubstituted Chromenes: J.C.S. Chem. Commun. 795 (1972).

    Google Scholar 

  92. Patel, B.P.J.: Citral Condensation: Towards Total Synthesis of Mahanimbine Isomers. Ind. J. Chem. 21B, 612 (1982).

    Google Scholar 

  93. Patel, B.P.J.: Cleaner Citral Condensation—Synthesis of Pyrano[2,3-a] Carbazoles. Synthetic Commun. 11, 823 (1981).

    CAS  Google Scholar 

  94. Patel, B.P.J.: Synthesis of Girinimbine Isomers—Pyrano [2,3-a] Carbazole Derivatives. Ind. J. Chem. 21B 20 (1982).

    CAS  Google Scholar 

  95. Patterson, A.M., and L.T. Capell: The Ring Index, p. 229, No 1675. New York: Reinhold. 1940.

    Google Scholar 

  96. Pecca, J.C., and S.M. Albonico: Trypnocides. I. Substituted 1,2,3,4-Tetrahydrocarbazoles. J. Med. Chem. 13, 327 (1970).

    CAS  Google Scholar 

  97. Pharr, D.Y., P.C. Uden, and S. Siggia: 3-(p-acetylphenoxy) Propyl Silane Bonded Phase for Liquid Chromatography of Basic Amines and Other Nitrogen Compounds. J. Chromat. Sci. 23, 391 (1985).

    CAS  Google Scholar 

  98. Pfeuffer, L., and U. Pindur: Diels-Alder-Reaktionen von 2’-substituierten-3vinyl-l-H-indolen zu neuen anellierten Indol-und Carbazole-Derivaten. Heiv. Chim. Acta 70, 1419 (1987).

    CAS  Google Scholar 

  99. Pindur, U.: New Diels-Alder Reactions with Vinylindoles: A Regio-and Stereo-controlled Access to Annelated Indoles and Derivatives. Heterocycles 27, 1253 (1988).

    CAS  Google Scholar 

  100. Pindur, U., and H. Erfanian-Ardoust: Indole 2,3 quinodimethanes and stable cyclic Analogues for Regio-and Stereocontrolled Syntheses of [b]-Annelated In-doles. Chem. Rev. 89, 1681 (1989).

    CAS  Google Scholar 

  101. Pindur, U., and L. Pfeuffer: [4+2]-Cyclo-addition to 4-Demethoxycarbazomycin. Heterocycles 26, 325 (1987).

    CAS  Google Scholar 

  102. Pindur, U., and L. Pfeuffer: New Structural Aspects of 3-Vinyl-IH-Indoles for Predicting the Outcome of Diels-Alder Reactions. Monatsh. Chem. 120, 27 (1989).

    Google Scholar 

  103. Pointek, J.A., and R.Y. Wang: Acute and Subchronic Effects of Rincazole (B234U) a Potential Antipsychotic Drug on A9 and A10 Dopamine Neurons in the Rat. Life Sci. 39, 651 (1986).

    Google Scholar 

  104. Raisz, L.G., C. Alander, C. Onklinkokx, and G.A. Rodan: Effects of Thiophen2-Carboxylic Acid and Related Compounds on Bone Resorption in Organ Culture. Calcif. Tissue Int. 37, 556 (1985) (C.A. 103, 206184s, 1985 ).

    Google Scholar 

  105. Rice, L.M., and K.R. Scot: 3-Substituted 1,2,3,4-Tetrahydrocarbazoles. J. Med. Chem. 13, 308 (1970).

    CAS  Google Scholar 

  106. Roy, S., A. Chakrabarti, and D.P. Chakraborty: Lewis Acid Catalysed Aliphatic Diazo-coupling. An Access to Nitrogen Heterocycles. Proc. Convention of Chemists (Ind. Chem. Soc.) C 34 (1986).

    Google Scholar 

  107. Roy, S., R. Guha, S. Ghosh, and D.P. Chakraborty: Biomimetic Hydroxylation Studies on Carbazole Alkaloids. Ind. J. Chem. 21B, 617 (1982).

    Google Scholar 

  108. Sakano, K., and S. Nakamura: New Antibiotics Carbazomycins A and B II. Structural Elucidations. J. Antibiotics 33, 961 (1980).

    CAS  Google Scholar 

  109. Saulnier, M.G., and C.W. Gribble: 4-Phenyl sulphonyl-4-H-Furo [3,4-b] Indole, a Stable Analogue of Indole-2,3-quinodimethane. Tetrahedron Letters, 5435 (1983).

    Google Scholar 

  110. Searl, A.J., F.C. Gee, and R.L. Wilson: In Oxygen radical in Chem. & Biol. (Proc. 3rd Int. Conf. 1983). (W. Bros, S. Manfered and C. Tait, Eds.) Berlin: David de Gruyter. (C.A. 100, 203140b, 1984 ).

    Google Scholar 

  111. Seaton, P.J., and S.J. Gould: New Products Related to Kinamycin from Streptomyces murayamaensis. Structures of Pre-Kinamycin, Keto-Anhydrokinamycin, and Kinamycins E and F. J. Antibiotics 42 189 (1989).

    CAS  Google Scholar 

  112. Seaton, P.J., and S.J. Gould: Kinamycin Biosynthesis Derivation by Excision of an Acetate Unit from a Single-chain Decaketide Intermediate. J. Amer. Chem. Soc. 109 5282 (1987).

    CAS  Google Scholar 

  113. Seaton, P.J., and S.J. Gould: Origin of Cyanamide Carbon of Kinamycin Antibiotics. J. Amer. Chem. Soc. 110 5912 (1988).

    CAS  Google Scholar 

  114. Sengupta, S.N.: Ph.D. Thesis, Calcutta University, 1979.

    Google Scholar 

  115. Sexton, W.A.: In: Chemical Constitution and Biological Activity, 3rd Edn., p. 306. London: F.N. Spon Ltd. 1973.

    Google Scholar 

  116. Shizuki, H., M. Kato, T. Ochiai, K. Matsui, and T. Morita: The Photochemical Rearrangements of N-Acetyl Diphenylamine and N-Acetyl Carbazole. Bull Chem. Soc., Japan 43, 67 (1970).

    Google Scholar 

  117. Sharma, K.S., and Sarita, CMR Spectral Studies of Substituted Carbazoles. Ind. J. Chem. 27B, 402 (1988).

    Google Scholar 

  118. Storch, E., H. Kirchner, K. Hueller, M.G. Maritinotti, and D. Gemsa: Enhancement by Carpofen or Indomethacin of Interferon Induction by 10Carboxymethyl-9-acridanone in Murine Cell Culture. J. Ger. Virol. 67, 1211 (1986) (C.A. 105, 35311r, 1986 ).

    Google Scholar 

  119. Stothers, J.B.: Carbon-13 NMR Spectroscopy, pp. 266. New York: Academic Press. 1972.

    Google Scholar 

  120. Tepaske, M.R., J.B. Gloer, D.T. Wicklow, and P.F. Dowd: An Antiviral Carbazole Alkaloid from Sclerotia of Aspergillus tubingensis. J. Org. Chem. 54, 4743 (1989).

    CAS  Google Scholar 

  121. Tepaske, M.R., J.B. Gloer, D.T. Wicklow, and P.F. Dowd: The Structure of Tubingensin B: A Cytotoxic Carbazole Alkaloid from Sclerotia of Aspergillus tubingensis. Tetrahedron Letters 30, 5965 (1989).

    CAS  Google Scholar 

  122. Torsi, A., M.P. Loria, G. Specchia, and D. Cassassima: In vitro Studies of Anti-inflammatory Activity of Carpofen. Eur. J. Rheumatol. Inflammation 5, 488 (1982) (C.A. 98, 46621e, 1983 ).

    Google Scholar 

  123. Udenfriend, S., C.T. Cark, J. Axelrod, and B.B. Brodu: Ascorbic Acid in Aromatic Hydroxylation I, a Model System of Aromatic Hydroxylation. J. Biol. Chem. 208, 731 (1954).

    CAS  Google Scholar 

  124. Wood, P.L., and P.S. Mcquade and S. Paul: Cyclindole and Flucindole Novel Tetrahydrocarbazoleamine Neuroleptics. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 8, 773 (1984) (C.A. 102, 125458 m, 1985 ).

    Google Scholar 

  125. Yamasaki, K., M. Kaneda, K. Watanabe, Y. Ueki, K. Ishamaru, S. Nakamura, R. Nomi, N. Yoshida, and T. Nakajima: New Antibiotics Carbazomycin A and B. III. J. Antibiotics 36, 552 (1983).

    CAS  Google Scholar 

Download references

Author information

Author notes

  1. D. P. Chakraborty

    Present address: , 11/1/5, Satchasipara Lane, Calcutta, 700 036, India

  2. Shyamali Roy

    Present address: , 18, J. N. Roy Lane, Calcutta, 700 006, India

Authors and Affiliations

  1. Comparative Phytochemical Laboratory, Bose Institute, Calcutta, India

    D. P. Chakraborty & Shyamali Roy

Authors
  1. D. P. Chakraborty
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shyamali Roy
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz

  2. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby

  3. Institut für Organische Chemie und Biochemie, Universität Bonn, Bonn, Federal Republic of Germany

    W. Steglich

  4. Institut für Organische Chemie, Universität Basel, Basel, Switzerland

    Ch. Tamm

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Springer-Verlag/Wien

About this chapter

Cite this chapter

Chakraborty, D.P., Roy, S. (1991). Carbazole Alkaloids III. In: Herz, W., Kirby, G.W., Steglich, W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 57. Springer, Vienna. https://doi.org/10.1007/978-3-7091-9119-4_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-9119-4_2

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-9121-7

  • Online ISBN: 978-3-7091-9119-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation